Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Synthesis and reactivity of bicyclo[3.2.1]octanoid-derived cyclopropanes.

Literature DB >> 22007996

Synthesis and reactivity of bicyclo[3.2.1]octanoid-derived cyclopropanes.

John R Goodell¹, Jennifer L Poole, Aaron B Beeler, Jeffrey Aubé, John A Porco.

Abstract

Photochemical oxa-di-π-methane rearrangement of bicyclo[3.2.1]octanoid scaffolds affords multifunctional, donor-acceptor cyclopropanes. A related photochemical reaction of an iminium ether substrate uncovered an unprecedented aza-di-π-methane rearrangement of a β,γ-unsaturated iminium. Donor-acceptor cyclopropanes have been evaluated as substrates for reactions generating several new chemotypes.

Entities: CellLine Chemical Disease Gene Species

Mesh：

Substances：

Year: 2011 PMID： 22007996 PMCID： PMC3235415 DOI： 10.1021/jo2018922

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

18 in total

1. Synthetic Aspects of the Di-pi-methane Rearrangement.

Authors: Howard E. Zimmerman; Diego Armesto
Journal: Chem Rev Date: 1996-12-19 Impact factor: 60.622

2. Novel oxa-di-pi-methane and Norrish type I reactions in the S2 (pi,pi*) excited state of a series of beta,gamma-unsaturated ketones.

Authors: Diego Armesto; Maria J Ortiz; Antonia R Agarrabeitia; Mar Martín-Fontecha
Journal: Org Lett Date: 2005-06-23 Impact factor: 6.005

3. Tandem processes identified from reaction screening: nucleophilic addition to aryl N-phosphinylimines employing La(III)-TFAA activation.

Authors: Hidenori Kinoshita; Oscar J Ingham; Winnie W Ong; Aaron B Beeler; John A Porco
Journal: J Am Chem Soc Date: 2010-05-12 Impact factor: 15.419

4. Development of an automated microfluidic reaction platform for multidimensional screening: reaction discovery employing bicyclo[3.2.1]octanoid scaffolds.

Authors: John R Goodell; Jonathan P McMullen; Nikolay Zaborenko; Jason R Maloney; Chuan-Xing Ho; Klavs F Jensen; John A Porco; Aaron B Beeler
Journal: J Org Chem Date: 2009-08-21 Impact factor: 4.354

5. Reaction discovery using microfluidic-based multidimensional screening of polycyclic iminium ethers.

Authors: Jennifer L Treece; John R Goodell; David Vander Velde; John A Porco; Jeffrey Aubé
Journal: J Org Chem Date: 2010-03-19 Impact factor: 4.354

6. Formal [3 + 2] cycloadditions of donor-acceptor cyclopropanes and nitriles.

Authors: Ming Yu; Brian L Pagenkopf
Journal: J Am Chem Soc Date: 2003-07-09 Impact factor: 15.419

7. Nucleophilic addition to iminium ethers in the preparation of functionalized N-alkyl heterocycles.

Authors: Erik Fenster; Brenton T Smith; Vijaya Gracias; Gregory L Milligan; Jeffrey Aubé
Journal: J Org Chem Date: 2007-12-11 Impact factor: 4.354

8. Scope and mechanism for lewis acid-catalyzed cycloadditions of aldehydes and donor-acceptor cyclopropanes: evidence for a stereospecific intimate ion pair pathway.

Authors: Patrick D Pohlhaus; Shanina D Sanders; Andrew T Parsons; Wei Li; Jeffrey S Johnson
Journal: J Am Chem Soc Date: 2008-06-11 Impact factor: 15.419

Synthesis and reactivity of bicyclo[3.2.1]octanoid-derived cyclopropanes.

1. Synthetic Aspects of the Di-pi-methane Rearrangement.

2. Novel oxa-di-pi-methane and Norrish type I reactions in the S2 (pi,pi*) excited state of a series of beta,gamma-unsaturated ketones.

3. Tandem processes identified from reaction screening: nucleophilic addition to aryl N-phosphinylimines employing La(III)-TFAA activation.

4. Development of an automated microfluidic reaction platform for multidimensional screening: reaction discovery employing bicyclo[3.2.1]octanoid scaffolds.

5. Reaction discovery using microfluidic-based multidimensional screening of polycyclic iminium ethers.

6. Formal [3 + 2] cycloadditions of donor-acceptor cyclopropanes and nitriles.

7. Nucleophilic addition to iminium ethers in the preparation of functionalized N-alkyl heterocycles.

8. Scope and mechanism for lewis acid-catalyzed cycloadditions of aldehydes and donor-acceptor cyclopropanes: evidence for a stereospecific intimate ion pair pathway.

9. Oxa-di-pi-methane photochemical rearrangement of quinuclidinones. Synthesis of pyrrolizidinones.

10. C-2/c-3 annulation and C-2 alkylation of indoles with 2-alkoxycyclopropanoate esters.

1. Tandem dienone photorearrangement-cycloaddition for the rapid generation of molecular complexity.

2. Multidimensional reaction screening for photochemical transformations as a tool for discovering new chemotypes.